The invention relates to novel N-(heterocyclicaminocarbonyl) substituted thiophenesulfonamides which are useful as herbicides, and their method-of-use as general pre-emergence or post-emergence herbicides or plant growth regulants.
In U.S. Pat. No. 4,127,405, issued Nov. 28, 1978 to Levitt, herbicidal benzene- and thiophenesulfonylureas are disclosed.
U.S. Pat. No. 4,398,939, issued Aug. 16, 1983 to Levitt discloses herbicidal thiophenesulfonylureas substituted by alkyl, OCH.sub.3, NO.sub.2, halogen, or sulfamoyl groups.
European Patent Application (EP-A)-No. 30,142, published June 10, 1981 teaches herbicidal thiophenesulfonylureas bearing ortho-carboxylic acid ester groups as well as other derivatives of carboxylic acids.
European Patent Application (EP-A)-No. 64,804, published Nov. 17, 1982, discloses herbicidal thiophenesulfonylureas bearing ortho-alkylsulfonyl groups.
U.S. Pat. No. 4,319,627, issued July 5, 1983 to Levitt discloses benzothiophenesulfonylureas.
European Patent Application (EP-A)-No. 79,683, published May 25, 1983, teaches herbicidal sulfonylureas including those of the general formulae: ##STR1## wherein Q is O, S or SO.sub.2 ;
R.sub.2 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.3 is H or CH.sub.3 ; and PA1 R.sub.4 is H or CH.sub.3. PA1 R" is alkyl. PA1 G is O, S, NH or NCH.sub.3 ; PA1 W is O or S; PA1 R is H or CH.sub.3 ; PA1 R.sub.1 is H, F, Cl, Br, NO.sub.2, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, S(O).sub.p C.sub.1 -C.sub.3 alkyl, S(O).sub.p C.sub.1 -C.sub.3 haloalkyl, CO.sub.2 (C.sub.1 -C.sub.3 alkyl), CO.sub.2 (C.sub.1 -C.sub.3 haloalkyl), OCH.sub.2 CH.dbd.CHR.sub.a, OCH.sub.2 C.tbd.CR.sub.a, CO.sub.2 (CH.sub.2 CH.dbd.CHR.sub.a), CO.sub.2 (CH.sub.2 C.tbd.CR.sub.a) or SO.sub.2 NR.sub.b R.sub.c ; PA1 R.sub.1 ' is H, CH.sub.3, F or Cl; PA1 p is 0, 1 or 2; PA1 R.sub.a is H or CH.sub.3 ; PA1 R.sub.b is H, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 haloalkyl; PA1 R.sub.c is H, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 haloalkyl; PA1 A is ##STR7## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 -alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, ##STR8## W.sub.1 and W'.sub.1 are independently O or S; m is 2 or 3; PA1 R.sub.d is H or CH.sub.3 ; PA1 R.sub.e is C.sub.1 -C.sub.2 alkyl; PA1 R.sub.f is C.sub.1 -C.sub.2 alkyl; PA1 Z is CH, N, CCH.sub.3, CC.sub.2 H.sub.5, CCl or CBr; PA1 Z.sub.1 is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, OCF.sub.2 H, SCF.sub.2 H, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.3 is H or CH.sub.3 ; PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; and PA1 Y.sub.4 is CH.sub.3, OCH.sub.3 or OC.sub.2 H.sub.5 ; PA1 W.sub.2 is O or S; PA1 R.sub.2 is H, F, Cl or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.3 is H, F, Cl or CH.sub.3 ; PA1 R.sub.4 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.5 is H or CH.sub.3 ; PA1 R.sub.6 is H, R.sub.8, SR.sub.8, SO.sub.2 R.sub.8, OR.sub.8, C(O)R.sub.8, C(O)L, (CO).sub.2 OR.sub.8, (CO).sub.2 R.sub.8, C(O)NR.sub.9 R.sub.10, C(O)NRA, C(S)SR.sub.8, NH.sub.2, NR.sub.9 R.sub.10, OH, CN, P(O)R.sub.11 R.sub.12, P(S)R.sub.11 R.sub.12 or Si(CH.sub.3).sub.2 R.sub.13 ; PA1 R.sub.7 is H, C.sub.1 -C.sub.6 alkyl, Cl, Br, CN, NO.sub.2, SR.sub.13, SO.sub.2 R.sub.13, CO.sub.2 R.sub.13 or C(O)R.sub.13 ; PA1 R.sub.8 is C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyalkoxyalkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 epoxyalkyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or phenyl optionally substituted with R.sub.14 ; when R.sub.8 is C.sub.3 -C.sub.6 cycloalkyl or C.sub.4 -C.sub.7 cycloalkylalkyl, it may optionally be substituted by C.sub.1 -C.sub.4 alkyl, 1 to 3 atoms of Cl or F or 1 Br; when R.sub.8 is C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl or C.sub.2 -C.sub.10 alkynyl, it may optionally be substituted by one or more halogens and/or by (R.sub.15).sub.r provided that when r is 2, the values of R.sub.15 may be identical or different; PA1 R.sub.9 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.10 is H, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 haloalkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.6 cycloalkyl or phenyl substituted with R.sub.14 ; PA1 R.sub.11 and R.sub.12 are independently C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; PA1 R.sub.13 is C.sub.1 -C.sub.10 alkyl, benzyl or phenyl optionally substituted with R.sub.14 ; PA1 R.sub.14 is H, F, Cl, Br, CH.sub.3, OCH.sub.3, NO.sub.2, CN, SCH.sub.3, SO.sub.2 CH.sub.3 or CF.sub.3 ; PA1 R.sub.15 is OR.sub.10, OC(O)R.sub.10, OC(O)NR.sub.9 R.sub.10, OSO.sub.2 R.sub.10, OP(O)R.sub.11 R.sub.12, OSi(CH.sub.3).sub.2 R.sub.13, SR.sub.10, SOR.sub.10, SOR.sub.2 R.sub.10, SCN, CN, SP(O)R.sub.11 R.sub.12, SP(S)R.sub.11 R.sub.12, P(O)R.sub.11 R.sub.12, P(S)R.sub.11 R.sub.12, NR.sub.9 R.sub.10, N.sup.+ R.sub.9 R.sub.10 R.sub.13, NR.sub.9 C(O)R.sub.10, NR.sub.9 C(O)OR.sub.10, NR.sub.9 C(O)NR.sub.9 R.sub.10, NR.sub.9 SO.sub.2 R.sub.10, NR.sub.9 P(O)R.sub.11 R.sub.12, NR.sub.9 P(S)R.sub.11 R.sub.12, NO.sub.2, C(O)R.sub.10, C(O)OR.sub.10, C(O)NR.sub.9 R.sub.10, C(R.sub.10)=NOR.sub.12, naphthyl, L, phenyl optionally substituted with R.sub.14 and/or R.sub.16, ##STR10## R.sub.16 is H, F, Cl, Br, phenoxy optionally substituted with R.sub.14, or phenyl optionally substituted with R.sub.14 ; PA1 R.sub.17 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkoxycarbonyl, F, Cl or CN; PA1 R.sub.18 is H, CH.sub.3, C.sub.1 -C.sub.3 alkoxy, F, Cl or OH; or PA1 R.sub.17 and R.sub.18 may be taken together to form --OCH.sub.2 CH.sub.2 O-- or --OCH.sub.2 CH.sub.2 CH.sub.2 O--; PA1 R.sub.19 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.20 is H or CH.sub.3 ; PA1 R.sub.21 and R.sub.22 are independently H or CH.sub.3 ; PA1 R.sub.23 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.24 is H, F, Cl, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy; PA1 R.sub.25 is H, F, Cl or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.26 is H, F, Cl or C.sub.1 -C.sub.2 alkyl; PA1 R.sub.27 is H, F, Cl or CH.sub.3 ; PA1 R.sub.28 is H, C.sub.1 -C.sub.4 alkyl, Cl, Br, CN, NO.sub.2, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfonyl, C.sub.1 -C.sub.3 alkoxycarbonyl or C.sub.1 -C.sub.3 alkylcarbonyl; PA1 R.sub.29 is H, CH.sub.3, Cl or Br; PA1 R.sub.30 is H, CH.sub.3, Cl or Br; PA1 R.sub.31 is H or CH.sub.3 ; PA1 R.sub.32 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.33 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, F or Cl; PA1 L is a 5- or 6-membered aromatic heterocycle, a 5- or 6-membered dihydroaromatic heterocycle or a 5- or 6-membered tetrahydroaromatic heterocycle which contains 1-4 heteroatoms selected from 0-1 oxygen atoms, 0-1 sulfur atoms and/or 0-4 nitrogen atoms, with the proviso that oxygen and sulfur are only linked to each other if the sulfur is in the form of SO or SO.sub.2, and these heterocycles may optionally be substituted by 1-4 CH.sub.3, 1-2 OCH.sub.3, SCH.sub.3, Cl, N(CH.sub.3).sub.2 or CN groups or L is a 5- or 6-membered lactone, lactam or cycloalkanone which may optionally be substituted by 1-4 CH.sub.3 groups; PA1 n is 0 or 1; PA1 p' is 0, 1 or 2; PA1 q is 0 or 1; and PA1 r is 1 or 2; PA1 (a) when W is S, then R is H, A is A-1, Z is CH or N, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR11## (b) the total number of carbon atoms in R.sub.2 and R.sub.3 is less than or equal to 4; PA1 (c) when X is Cl, F, or Br, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 (d) when J is J.sub.1 or J.sub.2, then R.sub.2 and R.sub.3 are other than F or Cl; PA1 (e) the total number of carbons atoms in R.sub.4 and R.sub.5 is less than or equal to 4; PA1 (f) the total number of carbon atoms in R.sub.6 is less than or equal to 13; PA1 (g) when J is J.sub.5, J.sub.6, J.sub.27, J.sub.28, J.sub.29, J.sub.30, J.sub.31, J.sub.32, J.sub.33, J.sub.34, J.sub.41, J.sub.42, J.sub.43 or J.sub.44 and n is O, then R.sub.4 and/or R.sub.5 is H; PA1 (h) when J is J.sub.61 or J.sub.62 and n is 0, then R.sub.4 is H or CH.sub.3 ; PA1 (i) when X or Y is OCF.sub.2 H, then Z is CH; PA1 (j) when R.sub.17 is C.sub.1 -C.sub.3 alkoxy, then R.sub.18 is H, CH.sub.3 or C.sub.1 -C.sub.3 alkoxy; and when R.sub.18 is C.sub.1 -C.sub.3 alkoxy, then R.sub.17 is not F, or Cl; PA1 (k) when R.sub.18 is OH, then R.sub.17 is H or C.sub.1 -C.sub.3 alkyl; and PA1 (1) when the total number of carbon atoms of X and Y is greater than four, then the number of carbon atoms of R.sub.1 is less than or equal to two, and the number of carbon atoms of R.sub.6 is less than or equal to four; PA1 R is H; PA1 W is O; and PA1 G is O or S. PA1 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and PA1 Y is H, CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CH.sub.2 CH.sub.3, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 .tbd.CH, CH.sub.2 OCH.sub.2 CH.sub.3, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 SCH.sub.2 CH.sub.3, ##STR12## OCF.sub.2 H, SCF.sub.2 H, C.tbd.CH or C.tbd.CCH.sub.3 ; PA1 G is S; PA1 R.sub.1 is H, Cl, Br or CH.sub.3 ; PA1 R.sub.2 and R.sub.4 are H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.3 is H or CH.sub.3 ; PA1 R.sub.6 is H, R.sub.8, C(O)R.sub.8 or CO.sub.2 R.sub.8 ; PA1 R.sub.7 is H, C.sub.1 -C.sub.2 alkyl, Cl, Br, SC.sub.1 -C.sub.2 alkyl, SO.sub.2 C.sub.1 -C.sub.2 alkyl, CO.sub.2 C.sub.1 -C.sub.2 alkyl or C(O)C.sub.1 -C.sub.2 alkyl; PA1 R.sub.8 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 epoxyalkyl or C.sub.1 -C.sub.4 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfinyl, C.sub.1 -C.sub.2 alkylsulfonyl, CO.sub.2 (C.sub.1 -C.sub.2 alkyl), C(O)C.sub.1 -C.sub.2 alkyl, CN or OH. PA1 R.sub.17 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 alkoxycarbonyl; PA1 R.sub.18 is H, CH.sub.3, C.sub.1 -C.sub.2 alkoxy or OH; or PA1 R.sub.17 and R.sub.18 may be taken together to form --OCH.sub.2 CH.sub.2 O-- or --OCH.sub.2 CH.sub.2 CH.sub.2 O--; PA1 R.sub.28 is H, C.sub.1 -C.sub.3 alkyl, Cl, Br or NO.sub.2 ; and PA1 R.sub.33 is H or CH.sub.3. PA1 A is A-1; PA1 Z is CH or N; PA1 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3 ; and PA1 Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2 ;
EPA-No. 107,979, published May 9, 1984, teaches herbicidal sulfonylureas including those of the general formulae: ##STR2## wherein .circle.S is ##STR3## n is 0, 1 or 2; G is O or NR"; and
South African Patent Application No. 83/5165 (Swiss priority 7/16/82, published 1/16/84) discloses herbicidal sulfonamides of formula ##STR4## wherein A is an unsubstituted or substituted bridge of 3 or 4 atoms which contains 1 or 2 oxygen, sulfur or nitrogen atoms and, together with the linking carbon atom, forms a non-aromatic 5- or 6-membered heterocyclic ring system, with the proviso that two oxygen atoms are separated by at least one carbon atom and that oxygen and sulfur atoms are only linked to each other if the sulfur atom takes the form of the --SO-- or SO.sub.2 -- group.